Undercover Boss: Kendall-Jackson CEO Pours it On

Five minutes into an advance screener of tomorrow’s Undercover Boss episode, all I wanted was a box of Kleenex and a hefty pour of Merlot.

If you haven’t seen the show (season three premiered Jan. 15 on CBS), the idea is this: A company’s senior executive does a Donnie Brasco, going underground to gain entry to hostile territory. That “hostile territory,” of course, is the nether regions of the company, the assembly lines and sales offices where regular folks make a living, far removed from the private-helicopter world of top management. Or so it seems.

The premise is that spending a week outside the nicely furnished management bubble will tell a CEO what’s fundamentally wrong with his or her organization—not who’s pilfering the Sharpies, but how the company’s strayed from its founding goals, and how that’s messing up business. In the end—guess what?—we find out we’re all the same, despite shocking income inequalities that are never mentioned. And that our common humanity, while it can’t exactly redeem capitalism, can at least offer a hell of a PR boost.

It’s as creaky and irresistible a premise as The Prince and the Pauper, only it makes you cry more. As I watched the January 29 episode, in which Kendall-Jackson Winery president Rick Tigner pretends to be a Texas grocery-store manager considering a career leap into wine, I forced my own willing suspension of cynicism.

The show had me at “drug overdose.” Tigner, who last year took over from Kendall-Jackson’s late founder Jess Jackson, grew up in modest circumstances. (His dad OD’d when Tigner was a kid.) Also, Tigner’s wife suffers from Parkinson’s disease, and he fears the half-a-billion-dollar wine megalith under his benevolent stewardship will lose its way now that Jackson is no longer around.

Tigner’s physical transformation (call it a makeunder) takes him from handsome, gray-templed CEO in button-down oxford to Jake Williams, a NASCAR dad with a Hulk Hogan mustache, a Kenny Chesney hat, and a Borat sense of the absurd only Tigner doesn’t seem to get (Jake is supposedly being filmed for a show about career changers).

Jake fumbles in the vineyard, where the stoic, Spanish-speaking workers seem to know that he’s as phony as his ‘stache. He busts a Kendall-Jackson truck driver who delivers as many F-bombs as he does cases of Chardonnay, fakes an I Love Lucy assembly-line fail in the mobile bottling facility, and makes an emotional connection with the hard-luck manager of a tasting room. It’s all not quite as unbelievable as the notion of Mitt Romney sweating a pink slip from Bain Capital, but it isn’t entirely plausible either.

Since I promised not to deliver a spoiler, I can’t tell you how the show wraps up, how Tigner—Dockers restored, his boardroom face back on—reveals himself to the employees he met, or what he rewards them with, or even how he makes peace with Jackson’s ghost. (“A lot of company presidents fly at 100,000 feet,” Tigner told me in a phone interview about what he took away from the experience. “You have to fly at 3 feet.”) I can tell you the moral of the show, which is that the adversity all of us experience can make us better people, if we don’t let it make us all foulmouthed and bitter. And that having a workforce of better people who don’t swear is good for a company, or anyway, for spending an hour of TV time.